An extraordinary opportunity to create a landmark residence in one of Toronto's most prestigious neighbourhoods. Set on a prime, highly coveted west-facing lot, this offering sits on the iconic curved red cobblestone section of Glenayr Road - one of Forest Hill's most distinguished and sought-after streets, just moments from Forest Hill Village. The property boasts a rare and generous land parcel, beginning at 40 ft of frontage and widening to approximately 71 ft, with a depth of 172.6 ft and a total area of approximately 8,600+ sq ft, offering exceptional scale and presence. This unique offering comes with Committee of Adjustment approvals for a striking custom-designed three-storey estate by renowned architect Richard Wengle, envisioned at approximately 6,000+ sq ft above grade and over 10,000 sq ft of total living space. The proposed design showcases expansive principal rooms, an integral garage, and a resort-inspired outdoor setting complete with pool, cabana, and curated entertaining spaces. Full architectural plans have been thoughtfully prepared, presenting a rare opportunity to bring a sophisticated vision to life with much of the groundwork already in place. The existing residence has been extensively prepared, offering flexibility for those who wish to proceed with the approved new build or explore a tailored transformation of the current structure. For the discerning builder, investor, or end-user, this is a rare chance to secure a premier property and step into an advanced-stage luxury project in an exceptional location. Property and improvements being sold in as-is, where-is condition. The current home has been demo'd back to the brick and is not liveable.
About this home
Photos of 42 Glenayr Road
Facts and features of 42 Glenayr Road
| Type | Detached |
|---|---|
| Style | 2-Storey |
| Bedrooms | 4 + 1 |
| Bathrooms | 4 |
| Size | 2000-2500 sq ft |
| Lot | 40 x 159.41 Feet |
| Parking | 7 |
| Garage | Attached |
| Heating | Water |
| Cooling | Central Air |
| Basement | Unfinished |
| Exterior | Brick |
| Taxes | $18,316 (2026) |
| Days on market | 178 |
| Listing brokerage | CHESTNUT PARK REAL ESTATE LIMITED |
Rooms
11 rooms, with sizes
| Room | Level | Size | Features |
|---|---|---|---|
| Recreation | Lower | 0′ 0″ × 0′ 0″ 0.0 × 0.0 m | |
| Kitchen | Main | 0′ 0″ × 0′ 0″ 0.0 × 0.0 m | |
| Furnace Room | Lower | 0′ 0″ × 0′ 0″ 0.0 × 0.0 m | |
| Dining Room | Main | 0′ 0″ × 0′ 0″ 0.0 × 0.0 m | |
| Living Room | Main | 0′ 0″ × 0′ 0″ 0.0 × 0.0 m | |
| Bedroom 2 | Second | 0′ 0″ × 0′ 0″ 0.0 × 0.0 m | |
| Primary Bedroom | Second | 0′ 0″ × 0′ 0″ 0.0 × 0.0 m | |
| Other | Lower | 0′ 0″ × 0′ 0″ 0.0 × 0.0 m | |
| Bedroom 3 | Second | 0′ 0″ × 0′ 0″ 0.0 × 0.0 m | |
| Library | Main | 0′ 0″ × 0′ 0″ 0.0 × 0.0 m | |
| Laundry | Lower | 0′ 0″ × 0′ 0″ 0.0 × 0.0 m |
Around this home
What’s near 42 Glenayr Road
From 42 Glenayr Road, the nearest station is St Clair West station (Line 1 Yonge-University), 17 minutes on foot; the nearest grocery store is Kitchen Table, 9 minutes on foot; the nearest TDSB elementary school is Forest Hill Junior and Senior Public School, 9 minutes on foot; and the nearest park is Vesta Parkette, 3 minutes on foot.
Transit
- St Clair West station Line 1 Yonge-University 17 min walk 5 min drive
- Forest Hill station Line 5 Eglinton 17 min walk 4 min drive
- Chaplin station Line 5 Eglinton 19 min walk 4 min drive
Groceries and pharmacies
- Kitchen Table Grocery 9 min walk
- Apotheca Compounding Pharmacy Pharmacy 9 min walk
- Rexall Pharmacy 9 min walk
- Loblaws Grocery 15 min walk
- Loblaws Grocery 15 min walk
Parks
- Vesta Parkette Park 3 min walk
- Ridgewood Parkette Park 5 min walk
- Suydam Park Park 7 min walk
Schools
- Forest Hill Junior and Senior Public School TDSB elementary · JK-8 EQAO 2024-25: Gr 6 reading 94% · Gr 6 math 90% 9 min walk
- Humewood Community School TDSB elementary · JK-8 EQAO 2024-25: Gr 6 reading 87% · Gr 6 math 60% 19 min walk 6 min drive
- Winona Drive Senior Public School TDSB middle school · 7-8 33 min walk 7 min drive
- Holy Rosary Catholic School Catholic elementary · JK-8 EQAO 2024-25: Gr 6 reading 100% · Gr 6 math 55% 12 min walk
- Forest Hill Collegiate Institute TDSB secondary · 9-12 EQAO 2024-25: Gr 9 math 60% · Gr 10 literacy 93% 19 min walk 5 min drive
- Marshall McLuhan Catholic Secondary School Catholic secondary · 9-12 EQAO 2024-25: Gr 9 math 59% · Gr 10 literacy 89% 31 min walk 7 min drive
Nearest schools, not necessarily the ones that serve this address. Check with the TDSB and TCDSB school locators.
Community
- Wychwood Library Library 16 min walk 4 min drive
- Chabad of Midtown Community Centre Community centre 17 min walk 4 min drive
- Phil White Arena Pool or arena 17 min walk 10 min drive
Private schools
- Girls
- The Bishop Strachan School JK to Grade 12 11 min walk
- Boys
- St. Michael's College School Grades 7 to 12 17 min walk 3 min drive
- Upper Canada College JK to Grade 12 24 min walk 6 min drive
- Royal St. George's College Grades 3 to 12 35 min walk 8 min drive
- Co-ed
- Arrowsmith School Ages 6 and up 20 min walk 4 min drive
- The Mabin School JK to Grade 6 28 min walk 8 min drive
- The York School JK to Grade 12 29 min walk 7 min drive
- De La Salle College "Oaklands" Grades 5 to 12 30 min walk 9 min drive
Within a 40-minute walk, from our list of private schools in central Toronto (checked October 2026). Fees and admissions on each school’s site. See all private schools
Restaurants
- Edo-Ko Google reviews 9 min walk
- Banfi Google reviews 9 min walk
- Sushi Lovers Google reviews 9 min walk
- Mashu Mashu Google reviews 10 min walk
- Wilsetti Google reviews 10 min walk
Places: OpenStreetMap contributors, October 2026. Walking and driving times: openrouteservice. Schools: EQAO 2024-25, Ontario Ministry of Education.
Request a showing
42 Glenayr Road
Nearby, at a similar price
See more homes like this one
$3,990,000 110 days on market
204 Richview Avenue
Detached · Toronto, ON
Forest Hill
4+1 beds · 4 baths · 4 parking
2500-3000 sq ft
$4,995,000 35 days on market
266 Lonsdale Road
Detached · Toronto, ON
Forest Hill
4 beds · 5 baths · 5 parking
3000-3500 sq ft
$4,999,000 26 days on market
516 Vesta Drive
Detached · Toronto, ON
Forest Hill
4+1 beds · 6 baths · 6 parking
3500-5000 sq ft
$3,799,000 41 days on market
151 Dewbourne Avenue
Detached · Toronto, ON
Humewood-Cedarvale
4+1 beds · 6 baths · 3 parking
3000-3500 sq ft
$3,695,000 13 days on market
5 Braemar Avenue
Detached · Toronto, ON
Chaplin Estates
4+1 beds · 4 baths · 7 parking
3000-3500 sq ft
$4,998,000 5 days on market
1 Nina Street
Detached · Toronto, ON
Casa Loma
4+2 beds · 5 baths · 5 parking
3500-5000 sq ft
Ask a question
42 Glenayr Road
Listing information is deemed reliable but is not guaranteed accurate by PropTx or the Toronto Regional Real Estate Board. Data source: PropTx. Listings are refreshed from the MLS® at least daily.
The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate and may not be used for any commercial purpose or any other purpose.
Royal LePage Terrequity Seymour Real Estate, Brokerage. Independently owned and operated.
MLS® C13081206 Data source: PropTx Listed May 4, 2026
